General, Organic, and Biological Chemistry STRUCTURES OF LIFE This page intentionally left blank General, Organic, and Biological Chemistry STRUCTURES OF LIFE Sixth Edition Karen Timberlake Contributions by MaryKay Orgill, Ph.D. University of Nevada, Las Vegas @ Pearson 330 I Judson Street, !XV NY 10013 Courseware Portfolio Manager: Scott Dustan Design Manager: Maria Guglielmo Walsh Director, Courseware Portfolio Management: Jeanne Zalesky Cover and Interior Designer: Tamara Newnam Content Producer: Melanie Field Courseware Portfolio Analyst, Content Dewlopment, Art: Jay McElroy Managing Producer: Kristen Rathman Photo and IIJustration Project Manager: Stephanie Marquez. 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Inc. or iL~ affiliates, authors, Hcensees or distributors. Library of Congress Cataloging-in-Publication Data Names: Timberlake, Karen C .. author. I Orgill, Mary Kay. 1974- Title: General, organic. and biological chemistry : structures of life I Karen Timberlake; contributions by Mary Kay Orgill. Ph.D., profe.ssor of chemistry. University of Nevada. Las Vega'i. Description: Sixth edition. I San Fr.mcisco. CA : Pearson Education. Inc., c2019. Identifiers: LCCN201704170211SBN 9780134730684 (hardcover) I ISBN 0134730682 Subjecls: LCSH: Chemistry--Textbooks. Classification: LCC QD33.2 .T56 20 I 9 I DOC 540--dc23 LC record available at hups:l/locn.Joc.gov/20 I 704 I 702 18 ISBN-10: 0-134-73068-2 JSBN-13: 978-0-134-73068-4 @Pearson www.pearsonhighered.com 1 Chemistry in Our Lives 1 2 Chemistry and Measurements 26 3 Matter and Energy 63 4 Atoms and Elements 99 5 Nuclear Chemistry 145 6 Ionic and Molecular Compounds 174 7 Chemical Reactions and Quantities 223 8 Gases 275 9 Solutions 310 10 Reaction Rates and Chemical Equilibrium 355 11 Acids and Bases 382 12 Introduction to Organic Chemistry: Hydrocarbons 426 13 Alcohols, Phenols, Thiols, and Ethers 467 14 Aldehydes and Ketones 496 15 Carbohydrates 521 16 Carboxylic Acids and Esters 560 17 Lipids 586 18 Amines and Amides 624 19 Amino Acids and Proteins 660 20 Enzymes and Vitamins 688 21 Nucleic Acids and Protein Synthesis 721 22 Metabolic Pathways for Carbohydrates 764 23 Metabolism and Energy Production 802 24 Metabolic Pathways for Lipids and Amino Acids 825 v 1 CHEMISTRY LINK TO HEALTH Bone Density 51 CLINICAL UPDATE Greg's Visit with His Doctor 54 Concept Map 55 Chemistry Chapter Review 55 KeyTerms 56 in Our Lives Key Math Skill 56 Core Chemistry Skills 57 CAREER Forensic Scientist Understanding the Concepts 57 Additional Practice Problems 59 CLINICAL UPDATE Forensic Evidence Helps Solve Challenge Problems 60 the Crime 1 Answers 60 1.1 Chemistry and Chemicals 2 1.2 Scientific Method: Thinking Like a Scientist 3 3 CHEMISTRY LINK TO HEALTH Early Chemist: Paracelsus 4 1.3 Studying and learning Chemistry 5 Matter and 1.4 Key Math Skills for Chemistry 9 Energy 1.5 Writing Numbers in Scientific Notation 17 63 CLINICAL UPDATE Forensic Evidence Helps Solve the Crime 20 CAREER Dietitian 63 Concept Map 20 CLINICAL UPDATE A Diet and Exercise Program 63 Chapter Review 21 3.1 Classification of Matter 64 Key Terms 21 CHEMISTRY LINK TO HEALTH Breathing Key Math Skills 21 Mixtures 66 Understanding the Concepts 23 3.2 States and Properties of Matter 67 Additional Practice Problems 23 3.3 Temperature 70 Challenge Problems 24 Answers 24 CHEMISTRY LINK TO HEALTH Variation in Body Temperature 74 2 3.4 Energy 74 3.5 Energy and Nutrition 77 CHEMISTRY LINK TO HEALTH Losing and Gaining Chemistry and Weight 79 3.6 Specific Heat 80 Measurements 26 3.7 Changes of State 82 CHEMISTRY LINK TO HEALTH Steam Burns 87 CAREER Registered Nurse 26 CLINICAL UPDATE A Diet and Exercise Program 88 CLINICAL UPDATE Greg's Visit with His Doctor 26 Concept Map 89 2.1 Units of Measurement 27 Chapter Review 89 2.2 Measured Numbers and Significant Figures 30 KeyTerms 90 2.3 Significant Figures in Calculations 32 Core Chemistry Skills 91 2.4 Prefixes and Equalities 36 Understanding the Concepts 92 2.5 Writing Conversion Factors 40 Additional Practice Problems 93 Challenge Problems 95 2.6 Problem Solving Using Unit Conversion 44 Answers 95 CHEMISTRY LINK TO HEALTH Toxicology and Combining Ideas from Chapters 1 to 3 97 Risk-Benefit Assessment 47 Answers 98 2.7 Density 49 vi Contents vii 4 CHEMISTRY LINK TO THE ENVIRONMENT Dating Ancient Objects 161 5.5 Medical Applications Using Radioactivity 163 Atoms and CHEMISTRY LINK TO HEALTH Brachytherapy 165 5.6 Nuclear Fission and Fusion 166 Elements 99 CLINICAL UPDATE Cardiac Imaging Using a Radioisotope 168 CAREER Farmer 99 Concept Map 168 CLINICAL UPDATE Improving Crop Production 99 Chapter Review 169 4.1 Elements and Symbols 100 Key Terms 169 4.2 The Periodic Table 102 Core Chemistry Skills 170 Understanding the Concepts 170 CHEMISTRY LINK TO HEALTH Elements Essential Additional Practice Problems 171 to Health 105 Challenge Problems 172 4.3 The Atom 107 Answers 172 4.4 Atomic Number and Mass Number 110 CHEMISTRY LINK TO THE ENVIRONMENT Many 6 Forms of Carbon 111 4.5 Isotopes and Atomic Mass 113 4.6 Electron Energy levels 117 Ionic and CHEMISTRY LINK TO HEALTH Biological Reactions Molecular to UV Light 117 4.7 Electron Configurations 122 Compounds 4.8 Trends in Periodic Properties 129 174 CLINICAL UPDATE Improving Crop Production 135 CAREER Pharmacy Technician 174 Concept Map 136 CLINICAL UPDATE Compounds at the Chapter Review 136 Pharmacy 174 Key Terms 137 Core Chemistry Skills 138 6.1 Ions: Transfer of Electrons 175 Understanding the Concepts 139 CHEMISTRY LINK TO HEALTH Some Important Ions Additional Practice Problems 141 in the Body 179 Challenge Problems 142 6.2 Ionic Compounds 179 Answers 142 6.3 Naming and Writing Ionic Formulas 182 6.4 Polyatomic Ions 186 5 6.5 Molecular Compounds: Sharing Electrons 190 6.6 lewis Structures for Molecules and Nuclear Polyatomic Ions 194 6.7 Electronegativity and Bond Polarity 199 Chemistry 6.8 Shapes and Polarity of Molecules 202 145 6.9 Intermolecular Forces in Compounds 207 CAREER Radiation Technologist 145 CLINICAL UPDATE Compounds at the Pharmacy 210 CLINICAL UPDATE Cardiac Imaging Using a Radioisotope 145 Concept Map 210 5.1 Natural Radioactivity 146 Chapter Review 211 Key Terms 212 5.2 Nuclear Reactions 149 Core Chemistry Skills 212 CHEMISTRY LINK TO HEALTH Radon in Our Understanding the Concepts 214 Homes 151 Additional Practice Problems 215 5.3 Radiation Measurement 156 Challenge Problems 217 CHEMISTRY LINK TO HEALTH Radiation and Answers 218 Food 157 Combining Ideas from Chapters 4 to 6 221 5.4 Half-life of a Radioisotope 159 Answers 222 viii Contents 7 8.6 Volume and Moles (Avogadro's Law) 291 8.7 The Ideal Gas Law 293 CHEMISTRY LINK TO HEALTH Hyperbaric Chemical Chambers 296 8.8 Partial Pressures (Dalton's Law) 298 Reactions and CHEMISTRY LINK TO HEALTH Blood Gases 299 Quantities CLINICAL UPDATE Exercise-Induced Asthma 301 223 Concept Map 301 Chapter Review 301 CAREER Exercise Physiologist 223 Key Terms 302 CLINICAL UPDATE Improving Natalie's Overall Core Chemistry Skills 303 Fitness 223 Understanding the Concepts 304 7.1 Equations for Chemical Reactions 224 Additional Practice Problems 305 7.2 Types of Chemical Reactions 230 Challenge Problems 305 7.3 Oxidation-Reduction Reactions 235 Answers 306 Combining Ideas from Chapters 7 and 8 308 7.4 The Mole 238 Answers 309 7.5 Molar Mass 242 7.6 Calculations Using Molar Mass 245 7.7 Mole Relationships in Chemical Equations 248 7.8 Mass Calculations for Chemical Reactions 251 9 7.9 Limiting Reactants and Percent Yield 253 7.10 Energy in Chemical Reactions 258 CHEMISTRY LINK TO HEALTH Cold Packs and Solutions 310 Hot Packs 261 CLINICAL UPDATE Improving Natalie's Overall CAREER Dialysis Nurse 310 Fitness 262 CLINICAL UPDATE Using Dialysis for Renal Concept Map 263 Failure 310 Chapter Review 263 9.1 Solutions 311 Key Terms 264 CHEMISTRY LINK TO HEALTH Water in the Core Chemistry Skills 265 Body 312 Understanding the Concepts 267 Additional Practice Problems 269 9.2 Electrolytes and Nonelectrolytes 314 Challenge Problems 271 CHEMISTRY LINK TO HEALTH Electrolytes in Body Answers 273 Fluids 318 9.3 Solubility 319 8 CHEMISTRY LINK TO HEALTH Gout and Kidney Stones: Saturation in Body Fluids 320 9.4 Solution Concentrations and Reactions 325 Gases 275 9.5 Dilution of Solutions 335 9.6 Properties of Solutions 338 CAREER Respiratory Therapist 275 CHEMISTRY LINK TO HEALTH Dialysis by the CLINICAL UPDATE Exercise-Induced Asthma 275 Kidneys and the Artificial Kidney 344 8.1 Properties of Gases 276 CLINICAL UPDATE Using Dialysis for Renal CHEMISTRY LINK TO HEALTH Measuring Blood Failure 346 Pressure 280 Concept Map 347 8.2 Pressure and Volume (Boyle's Law) 281 Chapter Review 347 CHEMISTRY LINK TO HEALTH Pressure-Volume Key Terms 348 Relationship in Breathing 282 Core Chemistry Skills 349 Understanding the Concepts 350 8.3 Temperature and Volume (Charles's Law) 284 Additional Practice Problems 351 8.4 Temperature and Pressure (Gay-Lussac's Challenge Problems 352 Law) 286 Answers 353 8.5 The Combined Gas Law 289 Contents ix 10 CHEMISTRY LINK TO HEALTH Buffers in the Blood Plasma 412 CLINICAL UPDATE Acid Reflux Disease 414 Reaction Rates Concept Map 415 Chapter Review 416 and Chemical Key Terms 417 Key Math Skills 417 Equilibrium 355 Core Chemistry Skills 417 Understanding the Concepts 419 CAREER Neonatal Nurse 355 Additional Practice Problems 419 Challenge Problems 420 CLINICAL UPDATE An Iron-Rich Diet for Answers 421 Children's Anemia 355 Combining Ideas from Chapters 9 to 11 424 10.1 Rates of Reactions 356 Answers 425 10.2 Chemical Equilibrium 360 10.3 Equilibrium Constants 363 12 10.4 Using Equilibrium Constants 366 10.5 Changing Equilibrium Conditions: Le Chatelier's Introduction Principle 369 CHEMISTRY LINK TO HEALTH Oxygen-Hemoglobin to Organic Equilibrium and Hypoxia 372 CHEMISTRY LINK TO HEALTH Homeostasis: Chemistry: Regulation of Body Temperature 375 CLINICAL UPDATE An Iron-Rich Diet for Hydrocarbons Children's Anemia 376 426 Concept Map 377 CAREER Firefighter/Emergency Medical Chapter Review 377 Technician 426 Key Terms 378 Core Chemistry Skills 378 CLINICAL UPDATE Diane's Treatment in the Understanding the Concepts 379 Burn Unit 426 Additional Practice Problems 379 12.1 Organic Compounds 427 Challenge Problems 380 12.2 Alkanes 430 Answers 381 12.3 Alkanes with Substituents 433 12.4 Properties of Alkanes 438 11 12.5 Alkenes and Alkynes 441 12.6 Cis-Trans Isomers 444 Acids and CHEMISTRY LINK TO THE ENVIRONMENT Pheromones in Insect Communication 447 Bases CHEMISTRY LINK TO HEALTH Cis-Trans Isomers 382 for Night Vision 447 12.7 Addition Reactions for Alkenes 447 CAREER Clinical Laboratory Technician 382 CHEMISTRY LINK TO HEALTH Hydrogenation of CLINICAL UPDATE Acid Reflux Disease 382 Unsaturated Fats 449 11.1 Acids and Bases 383 12.8 Aromatic Compounds 453 11.2 Brensted-Lowry Acids and Bases 385 CHEMISTRY LINK TO HEALTH Some Common 11.3 Strengths of Acids and Bases 388 Aromatic Compounds 455 11.4 Dissociation of Weak Acids and Bases 393 CHEMISTRY LINK TO HEALTH Polycyclic Aromatic 11.5 Dissociation of Water 395 Hydrocarbons (PAHs) 456 11.6 The pH Scale 398 CLINICAL UPDATE Diane's Treatment in the CHEMISTRY LINK TO HEALTH Stomach Burn Unit 456 Acid, HCI 404 Concept Map 457 11.7 Reactions of Acids and Bases 405 Chapter Review 458 CHEMISTRY UNK TO HEALTH Antacids 407 Summary of Naming 459 11.8 Buffers 409 Summary of Reactions 459